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Retirement Planning Checklist: 6 Steps To Get Ready

Retirement planning is easier to finish once you break it into pieces you can check off. Here are the six that matter most.

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Get your plan moving

A retirement plan stops feeling overwhelming once you split it into pieces you can finish one at a time. The six steps below cover the ground that matters most: your budget, your Social Security timing, any pension, how your portfolio is positioned, your insurance coverage, and where you plan to live. Working through them now, while you still have room to adjust, beats scrambling the month before your last paycheck.

Step 1: build a retirement budget

Start by sketching out what you expect to spend once your paycheck stops. Few retirees spend the same amount every single year. Spending is often higher in the first active years of retirement, settles down once a routine sets in, then rises again later as health costs grow. A budget built around that pattern holds up far better than one flat number carried across 30 years.

Step 2: pin down your Social Security number

Set up a free account at ssa.gov to see your earnings history and an estimate of your future benefit. The Social Security Administration also offers a quick calculator showing how your monthly check changes depending on the age you file. That timing decision carries real weight: filing before your full retirement age can cut your benefit by roughly 30% for life. Married couples have extra decisions to make, since one spouse's filing age affects what the other, and eventually a surviving spouse, can collect. Our guides on Social Security claiming strategy and spousal benefits walk through the tradeoffs, and the Social Security claiming calculator runs the numbers against your own record.

Step 3: confirm your pension payout

If a pension will be part of your income, call your employer's human resources department or the plan administrator and get an actual monthly figure rather than a guess. If you are married, ask specifically about the survivor option. Many pensions trim your monthly payment somewhat in exchange for continuing a reduced payment to your spouse after you pass away. That tradeoff is worth understanding well before you file for benefits.

Step 4: rebalance your portfolio for retirement

As retirement approaches, most people benefit from shifting part of their savings toward a more conservative mix, giving up some growth potential in exchange for less exposure to a sharp downturn. What matters most in the first several years of retirement is not your portfolio's long-run average return, it is the order in which those returns show up. A market drop that lands right as you begin taking withdrawals can do far more damage than the same drop arriving a decade later. Our breakdown of sequence of returns risk walks through two retirees with identical average returns and very different outcomes, purely because of when the bad years hit.

Step 5: update your insurance coverage

Go through every policy you carry: homeowner's, life, long-term care and auto. If you need to trim your retirement budget, raising a deductible on one of these is often the easiest place to start. Health coverage deserves its own look if you plan to stop working before Medicare eligibility at 65. Depending on your household, you might stay on a working spouse's employer plan, elect COBRA through a former employer, use a retiree health benefit tied to a pension, or shop your state's exchange at healthcare.gov.

Step 6: decide where you will live

Housing is one of the largest variables in a retirement budget, especially if a mortgage is still part of the picture. If a move is on the table, renting in a new area for a season before committing can save you from an expensive mistake. It also pays to think further ahead: do you want to age in your current home, move into a 55-and-up community, or eventually need assisted living? Each path carries a different price tag, and planning for it now beats reacting to it later.

Turn the checklist into a plan

Working through these six steps gives you a clear picture of where your retirement income will come from and how your spending is likely to shift over time. That clarity is what turns a vague goal into a plan you can actually follow.

If you get through this list and the numbers do not line up the way you hoped, you have three real levers to pull: work a bit longer, spend somewhat less, or add a source of guaranteed income to close the gap. The sooner you know which lever you need, the more choices you have. A licensed strategist can go through your numbers with you at no cost and no obligation.

James Forren Warren

Written and reviewed by

James Forren Warren

Licensed Retirement Income Strategist · License #20551202

James Forren Warren is a licensed Retirement Income Strategist with Tax Free Wealth Plan. For the past five years he has helped individuals and families turn their savings into retirement income they can count on. He writes and reviews the annuity research on this site and keeps it plain: what a product does, what it costs you, and who it actually fits.

Sources

  1. Social Security Administration: my Social Security account
  2. Medicare.gov: eligibility and enrollment

Educational only, not investment, tax or legal advice. Tax Free Wealth Plan LLC is a licensed insurance agency, not a registered investment adviser or broker-dealer. Annuities are not bank deposits, are not FDIC insured and are not guaranteed by any government agency. Guarantees are backed solely by the claims-paying ability of the issuing insurance company. Features, rates and availability vary by state and change over time; the contract and disclosure documents govern.

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